The present invention relates to the use of certain bicyclic octane derivatives in altering organoleptic properties, such as flavors and aromas, and compositions suited to such uses, as well as to certain novel bicyclic octane derivatives and processes for preparing them.
A material having the structure ##SPC1##
(dioxolane-substituted 5-isopropyl-7-methylbicyclo-[2.2.2]-oct-7 -ene) has been sold by Societe Anonyme Des Establissements Roure Bertrand Fils Et Justin Dupont 17 Bis Rue Legendre Paris XVII.sup.e France under the name "Glycollierol" for use in perfumes. Dragoco, Gerberding & Co., GmbH, Holzminden, Federal Republic of Germany has sold a material having the structure ##SPC2##
(carbomethoxy-substituted 1,4-dimethyl-bicyclo-[2.2.2]-oct-5-ene) as a perfume ingredient with a patchouli, vetivert type odor, under the name "Mahogonate".
U.S. Pat. No. 2,957,906 broadly shows acyl- and carboalkoxy-substituted bicyclooctene, among the other bicyclic compounds for pesticide and agricultural uses, and U.S. Pat. No. 3,304,167 shows various norbornane (bicyclo-[2.2.1]-heptane) derivatives, including nitrile derivatives and certain of the materials are said to be herbicidally active.
Danishevsky et al, Chem. Comm. 1968, 1287, show 1,3,3-trimethyl-6-isobutylbicyclo-[2.2.2]-octan-2-one and Kealy et al, J. Org. Chem., 26, 987 (1961) demonstrate 1,3-dimethyl-3-ethylbicyclo-[2.2.2]-octane and the corresponding bicyclooct-5-ene. Orahovats et al, Collect. Czech. Chem. Comm., 35(3), 838 (1970) show 2-hydroxy- and 2-oxo-substituted 3-methylbicyclo-[2.2.2]-oct-5-ene and the corresponding bicyclooctane. Organic Reactions, IV, 66 states that Diels and Alder, Ann. 478, 137 (1937) prepared bicyclo-[2.2.2]-oct-5-ene-8-carboxaldehyde and that .alpha.-phellandrene, 2-isopropyl-5-methylbicyclo-[2.2.2]-oct-5-en-7- and 8-carboxaldehyde were prepared by Diels and Alder, Ann. 470, 62 (1929).
Morita et al, J. Org. Chem. 30, 533 (1965, show various alkylated 4-alkoxybicyclo-[2.2.2]-octan-2-ones, and Curtin et al, J. Am. Chem. Soc. 81, 622 (1959) show methylated bicyclo-[2.2.2]-oct-5-en-2-ones. Various other bicyclo-[2.2.2]-octane materials and methods for their preparation are demonstrated by Petrov, J. Gen. Chem. U.S.S.R. 11, 809 (1941); Selca et al, Ber. 75, 1379 (1942); Kenyon and Young, J. Chem. Soc. 263 (1941); Alder et al, Ann. 543,1 (1939); Tich et al, Collect. Czech. Chem. Comm. 35(2), 459 (1970); Kraus et al, Ann. 708, 127 (1967); Berson et al, J. Am. Chem. Soc. 80, 5010 (1964); Karanskil et al, Zh. obshchei Khim. 29, 2976; McDonald et al, J. Org. Chem. 35, 1250 (1970); Curtin et al, J. Am. Chem. Soc. 81, 662 (1959); Conroy et al, J. Am. Chem. Soc. 75, 2530 (1953) and 78, 2290 (1957); Curtin et al, J. Am. Chem. Soc. 79, 3156 (1957); Waring et al, J. Am. Chem. Soc. 86, 1454 (1964); Alder et al, Ber. 90, 1709 (1957); Cookson et al, J. Chem. Soc. 2302 (1956); Kamamato, Chem. Abst. 58, 2391f (1963); and Cimarusti et al, J. Am. Chem. Soc. 90, 113 (1968).
German Offenlegungsschrift 2,242,913 shows tricyclic alcohol, denominated "nordehydro-patchoulol", extracted from patchouli alcohol. Tricyclic compounds have also been prepared by Greuber et al, Helv. Chim. Acta 55, 526 (1972). Various preparative procedures for preparation of tricyclic materials are exhibited by Waring et al, J. Am. Chem. Soc. 86, 1454 (1964) and Blum et al, Synthesis No. 4, 195 (1972). Quinones and quinols have been prepared by Chambers et al, J. Chem. Soc. (London) 1804 (1959) and McClure, J. Org. Chem. 28, 69 (1963). Various cyclic derivatives are demonstrated by Alder et al, Ber. 90, 1709 (1957) and Day, Chem. Rev. 53, 167 (1953).